金边桑叶中矢车菊素-3-O-(2″-没食子酰基)-β-吡喃半乳糖苷的提取分离及结构鉴定
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摘要
采用醇提水沉法富集金边桑叶中的总花色苷,运用Sephadex LH-20凝胶柱色谱、制备型高效液相色谱等技术对花色苷主成分矢车菊素-3-O-(2″-没食子酰基)-β-吡喃半乳糖苷(Cy3galloylGa)进行分离,使用紫外光谱(UV)、超高效液相色谱-电喷雾串联质谱(UPLC-ESI-MS/MS)以及核磁共振波谱等技术对其结构进行鉴定,并利用薄层色谱、高效液相色谱等方法分析Cy3galloylGa纯度。结果表明,Cy3galloylGa纯度为97.3%,基本满足质量控制等相关研究的需要。
We extracted total anthocyanins from Acalypha widesiana leaves by a alcohol-extraction and water-precipitation method,and separated cyanidin-3-O-(2″-galloyl-β-galactopyranoside)(Cy3 galloylGa) by Sephadex LH-20 gel column chromatography and preparative high performance liquid chromatography.Furthermore,we characterized the structure of Cy3 galloylGa by UV spectrum,ultra-high performance liquid chromatography-electrospray ionization tandem mass spectrometry(UPLC-ESI-MS/MS),and nuclear magnetic resonance spectroscopy.Moreover,we analyzed the purity of Cy3 galloylGa by thin-layer chromatography(TLC) and HPLC.The results show that the purity of Cy3 galloylGa is 97.3%,which meets the basic needs of related research such as quality control.
We extracted total anthocyanins from Acalypha widesiana leaves by a alcohol-extraction and water-precipitation method,and separated cyanidin-3-O-(2″-galloyl-β-galactopyranoside)(Cy3 galloylGa) by Sephadex LH-20 gel column chromatography and preparative high performance liquid chromatography.Furthermore,we characterized the structure of Cy3 galloylGa by UV spectrum,ultra-high performance liquid chromatography-electrospray ionization tandem mass spectrometry(UPLC-ESI-MS/MS),and nuclear magnetic resonance spectroscopy.Moreover,we analyzed the purity of Cy3 galloylGa by thin-layer chromatography(TLC) and HPLC.The results show that the purity of Cy3 galloylGa is 97.3%,which meets the basic needs of related research such as quality control.
引文
[1] 中国科学院中国植物志编委会.中国植物志[M].第44卷第2分册.北京:科学出版社,1996:112.
[2] 王永泉,王德昌,徐丽珍.金边桑提取物抗肿瘤作用的实验观察(简报)[J].中国医学科学院学报,1991(5):371.
[3] ADESINA S K,IDOWU O,OGUNDAINI A O,et al.Antimicrobial constituents of the leaves of Acalypha wilkesiana and Acalypha hispida[J].Phytotherapy Research,2000,14(5):371-374.
[4] ALADE P I,IROBI O N.Antimicrobial activities of crude leaf extracts of Acalypha wilkesiana[J].Journal of Ethnopharmacology,1993,39(3):171-174.
[5] WU H T,PANG H Y,CHEN Y P,et al.Anti-inflammatory effect of a polyphenol-enriched fraction from Acalypha wilkesiana on lipopolysaccharide-stimulated RAW 264.7 macrophages and acetaminophen-induced liver injury in mice[J].Oxidative Medicine and Cellular Longevity,2018,7858094.
[6] 腾飞,郑悦,王萍.龙葵果花色苷的分离与鉴定[J].食品科学,2016,37(7):56-61.TENG F,ZHENG Y,WANG P.Isolation and identification of anthocyanins from Solanum nigrum L.fruits[J].Food Science,2016,37(7):56-61.
[7] STRACK D,WRAY V,METZGER J W,et al.Two anthocyanins acylated with gallic acid from the leaves of Victoria amazonica[J].Phytochemistry,1992,31(3):989-991.
[8] REIERSEN B,KIREMIRE B T,BYAMUKAMA R,et al.Anthocyanins acylated with gallic acid from chenille plant,Acalypha hispida[J].Phytochemistry,2003,64(4):867-871.
[9] 夏效东,凌文华,郑琳,等.HPLC法测定黑米皮提取物中花色苷成分及含量[J].食品科学,2006,27(2):206-208.XIA X D,LING W H,ZHENG L,et al.Determination of anthocyanin component and content in black rice extract by HPLC[J].Food Science,2006,27(2):206-208.
[10] 高慧,李长坤,李月琪.超高效液相色谱三重四极杆质谱联用法测定蔬菜中的三十七种农药残留[J].食品安全导刊,2014(13):34-35.
[11] 卓毓光,刘儒华,古福生,等.花青素稳定性影响因素与应用研究进展[J].广东化工,2018,45(24):70-72.ZHUO Y G,LIU R H,GU F S,et al.The factors influencing anthocyanins stability and progress on application research[J].Guangdong Chemical Industry,2018,45(24):70-72.
[12] ABDEL-AAL E S M,HUCL P.Composition and stability of anthocyanins in blue-grained wheat[J].Journal of Agricultural and Food Chemistry,2003,51(8):2174-2180.
[13] 卢钰,董现义,杜景平,等.花色苷研究进展[J].山东农业大学学报(自然科学版),2004,35(2):315-320.LU Y,DONG X Y,DU J P,et al.Research progress on anthocyanins[J].Journal of Shandong Agricultural University(Natural Science Edition),2004,35(2):315-320.
[14] STEYN W J,WAND S J E,HOLCROFT D M,et al.Anthocyanins in vegetative tissues:a proposed unified function in photoprotection[J].New Phytologist,2002,155(3):349-361.
[15] FOSSEN T,SLIMESTAD R,?VSTEDAL D O,et al.Anthocyanins of grasses[J].Biochemical Systematics and Ecology,2002,30(9):855-864.
[16] van WYK B E,WINTER P J D.Chemotaxonomic value of anthocyanins in Podalyria and Virgilia(tribe Podalyrieae:Fabaceae)[J].Biochemical Systematics and Ecology,1994,22(8):813-818.
[17] 朱满兰,王亮生,张会金,等.耐寒睡莲花瓣中花青素苷组成及其与花色的关系[J].植物学报,2012,47(5):437-453.ZHU M L,WANG L S,ZHANG H J,et al.Relationship between the composition of anthocyanins and flower color variation in hardy water lily(Nymphaea spp.) cultivars[J].Bulletin of Botany,2012,47(5):437-453.
[2] 王永泉,王德昌,徐丽珍.金边桑提取物抗肿瘤作用的实验观察(简报)[J].中国医学科学院学报,1991(5):371.
[3] ADESINA S K,IDOWU O,OGUNDAINI A O,et al.Antimicrobial constituents of the leaves of Acalypha wilkesiana and Acalypha hispida[J].Phytotherapy Research,2000,14(5):371-374.
[4] ALADE P I,IROBI O N.Antimicrobial activities of crude leaf extracts of Acalypha wilkesiana[J].Journal of Ethnopharmacology,1993,39(3):171-174.
[5] WU H T,PANG H Y,CHEN Y P,et al.Anti-inflammatory effect of a polyphenol-enriched fraction from Acalypha wilkesiana on lipopolysaccharide-stimulated RAW 264.7 macrophages and acetaminophen-induced liver injury in mice[J].Oxidative Medicine and Cellular Longevity,2018,7858094.
[6] 腾飞,郑悦,王萍.龙葵果花色苷的分离与鉴定[J].食品科学,2016,37(7):56-61.TENG F,ZHENG Y,WANG P.Isolation and identification of anthocyanins from Solanum nigrum L.fruits[J].Food Science,2016,37(7):56-61.
[7] STRACK D,WRAY V,METZGER J W,et al.Two anthocyanins acylated with gallic acid from the leaves of Victoria amazonica[J].Phytochemistry,1992,31(3):989-991.
[8] REIERSEN B,KIREMIRE B T,BYAMUKAMA R,et al.Anthocyanins acylated with gallic acid from chenille plant,Acalypha hispida[J].Phytochemistry,2003,64(4):867-871.
[9] 夏效东,凌文华,郑琳,等.HPLC法测定黑米皮提取物中花色苷成分及含量[J].食品科学,2006,27(2):206-208.XIA X D,LING W H,ZHENG L,et al.Determination of anthocyanin component and content in black rice extract by HPLC[J].Food Science,2006,27(2):206-208.
[10] 高慧,李长坤,李月琪.超高效液相色谱三重四极杆质谱联用法测定蔬菜中的三十七种农药残留[J].食品安全导刊,2014(13):34-35.
[11] 卓毓光,刘儒华,古福生,等.花青素稳定性影响因素与应用研究进展[J].广东化工,2018,45(24):70-72.ZHUO Y G,LIU R H,GU F S,et al.The factors influencing anthocyanins stability and progress on application research[J].Guangdong Chemical Industry,2018,45(24):70-72.
[12] ABDEL-AAL E S M,HUCL P.Composition and stability of anthocyanins in blue-grained wheat[J].Journal of Agricultural and Food Chemistry,2003,51(8):2174-2180.
[13] 卢钰,董现义,杜景平,等.花色苷研究进展[J].山东农业大学学报(自然科学版),2004,35(2):315-320.LU Y,DONG X Y,DU J P,et al.Research progress on anthocyanins[J].Journal of Shandong Agricultural University(Natural Science Edition),2004,35(2):315-320.
[14] STEYN W J,WAND S J E,HOLCROFT D M,et al.Anthocyanins in vegetative tissues:a proposed unified function in photoprotection[J].New Phytologist,2002,155(3):349-361.
[15] FOSSEN T,SLIMESTAD R,?VSTEDAL D O,et al.Anthocyanins of grasses[J].Biochemical Systematics and Ecology,2002,30(9):855-864.
[16] van WYK B E,WINTER P J D.Chemotaxonomic value of anthocyanins in Podalyria and Virgilia(tribe Podalyrieae:Fabaceae)[J].Biochemical Systematics and Ecology,1994,22(8):813-818.
[17] 朱满兰,王亮生,张会金,等.耐寒睡莲花瓣中花青素苷组成及其与花色的关系[J].植物学报,2012,47(5):437-453.ZHU M L,WANG L S,ZHANG H J,et al.Relationship between the composition of anthocyanins and flower color variation in hardy water lily(Nymphaea spp.) cultivars[J].Bulletin of Botany,2012,47(5):437-453.